Synthesis of the C1-C12 acid fragment of amphidinolide T marine macrolides via SmI2-mediated enantioselective reductive coupling of aldehydes with a chiral crotonate |
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Authors: | Jialu Luo Jinlong Wu Wei-Min Dai |
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Affiliation: | a Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
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Abstract: | A new strategy for enantioselective assembly of the trisubstituted tetrahydrofuran ring has been established for synthesis of the C1-C12 acid fragment of amphidinolide T series marine macrolides. The key steps involve the SmI2-mediated highly enantioselective reductive coupling of an aldehyde with the (1S,2R)-N-methylephedrine-derived crotonate to form the cis-3,4-disubstituted γ-butyrolactone and the subsequent BF3-mediated 1,3-anti-selective allylation of the five-membered-ring oxocarbenium ion with allyltrimethylsilane. The desired C1-C12 acid fragment was obtained in >25% overall yield via a 9-step sequence. |
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Keywords: | Allylation Amphidinolide γ-Butyrolactone Macrolide Samarium |
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